


The Mad Ones

by supershadowlocked



Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - High School, Angst with a Happy Ending, Best Friends, Childhood Friends, Dean is a Little Shit, F/M, Friends With Benefits, Friends to Lovers, Harvelle's Roadhouse, Lacrosse, M/M, Maybe someone dies, Neighbors, Road Trips, Sexy Times, Sexy car wash, Sharing a Bed, Threesome - F/F/M, Threesome - F/M/M
Language: English
Status: In-Progress
Published: 2015-07-17
Updated: 2015-09-26
Packaged: 2018-04-09 18:24:30
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 19,514
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4359542
Author URL: https://archiveofourown.org/users/supershadowlocked/pseuds/supershadowlocked
Summary: <blockquote class="userstuff">
              <p>They've been best friends and neighbors for years. Their families are practically merged together. So what if Cas is having some unwelcome, dangerous thoughts about his best friend. It'll blow over, right?<br/>/I suck at summaries. Will fix later./</p>
            </blockquote>





	1. Prologue

2006  
11 years old  
The for sale sign next to Dean's house got knocked down the summer of '01. He remembered that day clearly—the oppressive humidity condensing on their sticky skin as they downed Cokes and lemonades and ice waters in a desperate attempt to keep cool. Jo came over that day to play, blonde hair secured in twin braids, and they sat together on the cement steps leading up to the Winchester's front door. The gnarled tree in the yard provided limited shade—that is, none. If you were exactly three inches wide, you could try to stand under the shadow of one of the naked branches.

Instead, Jo and Dean were sprawled on the uncomfortable steps, bikes forgotten, because even outside was better than the stuffy indoors. Broken air conditioners in the Midwest were punishments delivered by the devil himself, and Dean wasn't sure who in his family must have made a deal with a demon to bring them such pain. He wouldn't put it past them.

Dean was just starting to suggest they walk to the gas station on the corner for a reprieve from the sweltering heat and some slurpees when a U-Haul truck rolled up to the empty house right beside the Winchester's. The two friends watched with interest as a gold '78 Lincoln Continental Mark V and, contrastingly, a white minivan, followed closely behind. 

"Looks like you got new neighbors," Jo noted, fanning herself futilely with her the daily newspaper. Dean almost didn't want to bring in the newspaper—each day brought worsening news about the fighting in Iraq and other parts of the Middle East. Dean didn't understand it all, but he did understand the frustration and pain it brought to his veteran marine father.

Dean scrunched up his nose. "Hopefully they aren't freaks."

Jo raised her eyebrows. "Right, because your family is perfectly normal."

Dean rolled his eyes and continued to observe the new disturbance next door through the oak trees. He watched as a disgruntled looking man stepped out of the Lincoln and squinted up at the house before pulling out a flask. His graying hair was messy, his beard scraggly and untrimmed, and he wore, strangely, a bath robe over his clothes.

Gradually, five kids followed, eyeing their new home with varying levels of excitement and apprehension. 

Five kids, and Dean only noticed one.

He looked about Dean's age, small but not scrawny, messy dark hair, and squinting eyes. His head turned and he caught Dean's gaze unwaveringly, a move that led to somewhat of a staring contest between the two of them. 

But then Mary burst out of the house, long hair tied messily away from her face, plate of cookies in hand. She nearly tripped over Dean, catching the cookies just before they slid out of her grasp. 

"Dean! I'm so glad you're here. You can come say hi with me."

There really was no room for argument, so the eleven year old pushed off from the cement, grimacing at the sweat spots left behind. Jo laughed at him, promising to wait for his return. And so Dean trotted after his determined mom, curiosity over the new family propelling him forward. 

"Hi there!" She called cheerfully.

The man who'd drank from the flask earlier turned around, tired eyes landing on Mary Winchester and her prepared plate of cookies. He offered a tentative smile that looked more terrified than happy.

"Uh, hello. Hi," he started awkwardly, voice slightly shaky and higher in pitch.

Unfazed, Mary extended the dessert out to him, which the man tentatively accepted, before she placed a hand on Dean's shoulder. "My name is Mary Winchester. I live next door. This is my son, Dean. He's eleven. My husband and other son aren't home at the moment."

Chuck nodded a couple times. "Hi, I'm—I'm Chuck Shurley. These are my kids, uh—"

A young redhead stepped forward, apparently trying to save her father the pain of introductions. "I'm Anna! That's Michael," she pointed to the oldest who nodded curtly in greeting, "Gabe," a short kid munching on a Snickers grinned at Dean, "Luke," she gestured to a sulking blonde who lurked a few feet away from the rest of them, "and Castiel. He's eleven too! I'm ten." 

Dean's eyes snapped to the blue eyed boy who was still staring at him. Castiel. He had a name. A friggin' weird name, but a name nonetheless.

"My friend Jo is over, if you wanna meet her," Dean suggested to Castiel and Anna since they were his closest in age.

Anna beamed. "Of course we wanna! Come on, Castiel," she grabbed her brother's arm, nearly yanking it off as she motioned to Dean to lead the way.

Jo stood as the newcomers approached, pleasant as ever when she smiled in the way that pushed her cheeks up and made her look like the most innocent girl you'd ever met. Dean, of course, knew better. He'd seen her arm wrestle a grown man, shoot a raccoon eating her mom's garden, and even punch Dean a few times with more force than necessary. 

Castiel seemed a bit awkward with the introductions, unsure of how to respond. He stuck his arm out for a formal handshake, and Jo took one look at it before bursting out laughing. The confusion on Castiel's face was priceless, and even Anna, who'd grown more shy around Anna, joined in the giggling. 

"Hey, now we have enough people to play dodgeball!" Dean said excitedly.

Jo huffed at him. "We do not. There's only four of us!" 

"So? Better than just you and me hitting each other with balls."

"Not sure I agree with you on that one," Jo said thoughtfully. Dean didn't even have time to react before Jo had picked up an abandoned soccer ball and lobbed it at his knees.

Castiel furrowed his brow. "I'm not sure I understand the object of this game."

With as serious a face as he could muster, Dean picked up the soccer ball and tossed it lightly up and down. "In the game of dodgeball," he began dramatically, earning a giggle from Anna, "you either win, or you lose. There is no in between. In fact, there's only one rule."

He paused for effect, waiting for the blue eyed boy to take the bait.

Castiel bit. "And what's that?"

"Dodge," Dean said solemnly, face impassive as he launched the ball at Castiel. The boy dropped like a deadweight, and Dean was worried for a second that he'd scare him away.

But then Castiel glanced up, and Dean recognized the look in his eyes. He'd encountered it too many times with Jo.

Dean was once again the receiving end of the ball's trajectory, and he clutched his stomach, moaning. "Okay, okay. I think we all understand the game," he glanced at Castiel, "And if you can't best 'em, join 'em." 

And so they divided into two teams, boys against girls. Jo was vicious in her offense, but she was no match for Dean and Castiel together. They played until the light trickled away and Jo had to get home to her mother, Ellen. 

Before Castiel could follow Anna to their house, Dean stuck out his hand. "Truce?"

His new neighbor eyed Dean's hand thoughtfully before grinning mischievously. "Never."

Dean stared in fascination and newfound respect as Cas—because Castiel was just a mouthful—jogged off into the cover of the trees. He decided he liked the strange, blue eyed boy, and he chose to believe he'd made a new friend. 

Dean remembered that name, Castiel, for the rest of the night—he couldn't get it out of his head. The name bounced around his mind as he stirred his peas at dinner, as he brushed his teeth that night, and as he lie in bed.

"Castiel," he whispered to the silent night, rolling the syllables around on his tongue. 

He was sticking with Cas: less formal, less letters. 

The name floated out his open window soundlessly and into Castiel's directly across the yard. The blue eyed boy settled into an air mattress in his brand new room with its creaking floors and ugly leaf wallpaper. He had a house, but it wasn't a home. Yet.

Still, he fell asleep with a new name attached to a freckled, green eyed boy that kept resurfacing.

"Dean," he said quietly to the empty room.


	2. The Taste

**Summary for the Chapter:**

> Dean and Cas discuss girls and Satan's cooking...

2010  
15 years old

"Okay, what about April Kelly?" Dean stared down at his first ever high school yearbook propped on his thighs, flipping through the glossy pages decorated with pictures of classmates he couldn't care less about. Freshman year had just ended, and Dean decided it was time to actively seek out girls sophomore year. 

"Not interested," came the reply from the bed Dean was leaning his back against.

Craning his neck around in disbelief, Dean found his best friend lying with his face trained on the ceiling, tossing a lacrosse ball up and down.

"Not interested? Dude, April is hot. Plus she totally has that I'm-sexy-but-also-smart-and-I-help-out-the-homeless-in-my-spare-time kind of vibe. You know, seems like your type." 

Cas took his eyes off the ball for a second to glare at Dean before resuming his activity. "So what, exactly, do you propose I do, Dean? Shall I impersonate a homeless man to 'get in her pants'?" 

Dean could practically hear the air quotes in his friend's question. Grinning, he shrugged. "Hey, I hadn't thought of that. Not a bad idea though—"

Cas whacked Dean on the head with his lacrosse ball. "I'm not going to dupe some nice girl into performing sexual activities solely for my pleasure." 

"Solely for your pleasure? Trust me, she'll get something out of it too."

The thunking against the ceiling stopped for a moment. "Not necessarily. It's not like I have experience in that sort of thing."

Staring at April's smiling face in the yearbook, Dean smirked. "I'm sure she'd be an excellent teacher."

Cas sighed and continued to toss the ball in the air. Dean decided it was time for a topic change, and he shut the book before standing to sit on Cas's bed, pressing his back against the wall. The mattress sunk under his weight, and Cas almost missed the ball as it came down.

"You gonna try out for lacrosse this year?" He followed the ball's movements with his eyes.

"I am not sure."

"Dude, you'd totally make the team. Just try out. I have full confidence that you'll make the cut. And if for some crazy reason you don't, then at least you will have tried, right?"

The ball's movements finally ceased and Cas propped himself up on his forearms. "You really think so?"

Dean searched Cas's eyes. "Of course. Why would I lie about that? You've got a great build—I know you're strong. Plus, you have a hidden warrior side."  
Cas blushed slightly, but his lips quirked upwards. "'Great build'? 'Hidden warrior side'?" 

Dean matched his smile. "Oh yeah. I've seen you take on your brothers. I swear, if it wasn't for Anna, you would've all killed each other by now. And," he added, a mischievous glint in his eyes, "I'll bet April would love to get her hands on that great build."

Cas blushed darker, but there was something else in his eyes besides embarrassment. Disappointment maybe? Dean couldn't tell, and before he could analyze it, Cas's expression smoothed over. He shook his head fondly, avoiding the April subject entirely. "Anna is something special alright."

The redhead picked that moment to peak inside Cas's room. "Dinner's ready!"

"Who made it?" Castiel asked suspiciously.

"Lucifer," Anna replied, a smile teasing her lips. Cas once told Dean, in the rare moments he spoke of his mother, that she had picked the name because of her fascination with the angels. Her defense of the name was that Lucifer wasn't afraid to stand up for what he believed in, that he wasn't easily intimidated, and he made his choices based on love. Seemed a bit of a stretch to Dean, but he wasn't going to dare say anything that could go against the beloved mother of the Miltons. 

That being said, Dean still didn't understand how someone described so admiringly could have found herself with a man like Chuck. Not that the Miltons' father was a monster or anything. He'd just sunk into fits of drunken despair and abandoned his family. 

And yet, all the kids defended him in a heartbeat. Paternal loyalty. Or, perhaps, just general familial loyalty. Dean understood more than anyone, more than Sam. He'd always been loyal to his father, hanging on to John Winchester's every word, especially as a child. Hell, he'd even inherited John's taste in music, cars, and leather. Now guns, that was just a given if you were a native Kansan.

Dean groaned. "For all I know, Satan has baked us all rolls with razor blades inside."

Anna rolled her eyes at him. "Luc is just chasing his dream of becoming a professional chef. His food isn't half bad. Today it's spicy chili. Boiled with the blood of infants."

"Well, he always has had a flair for the dramatic. Should we name it the soup from hell?" Dean grumbled sarcastically. 

Cas coughed to hide his laugh, and Anna raised her eyebrows. "Chili isn't a soup, really—"

"But all that boiled blood would give it more of a watery consistency, right? So, in this case, soup," Dean built on the argument.

"Blood is thicker than water," Anna threw at him.

"I don't think that's supposed to be in reference to nourishment," Cas jutted in.

"Oh whatever. I'd probably draw the line at cannibalism, but I just want some damn food. If I have to die, food is the only way to go out."

"Fitting," Cas added, "Although I see your demise brought on by a nice pecan pie rather than chili. More poetic."

Dean stared at Cas in mock horror. "How dare you! Don't bring pie into this; she didn't do anything."

"She?" 

"Second only to dad's Impala, pecan pie is the love of my life. Then there's bacon cheeseburgers, and of course my favorite pistol," Dean faked a moan, rubbing his stomach. Cas, unable to stop the furious blushing, stared determinedly at his hands instead of his best friend who was currently making obscene noises. 

"Okay, okay. This needs to stop before you sport a damn hard on," Anna interrupted, hands held in front of her as she slowly backed out the door.

"Anna! Don't say things like that," Castiel gasped, obviously horrified at his younger sister's language. And all too aware of the possibility of his own.

She raised an eyebrow and crossed her arms. "What? I'm not stupid. I'm—"

"Thirteen. Yeah, we know."

"Fourteen," she corrected him exasperatedly.

Dean snickered at the sibling banter that was all too similar to his and Sam's, except for the fact that Anna and Cas were so much closer in age. "We'll see if Satan's cooking can compare."

 

Later that night, after his best friend had gone home to the house next door, Castiel definitely did not think back to those noises Dean had been making.

He most definitely did not think about other circumstances in which Dean would voice similar sounds.

And he definitely did not dream about Dean making those noises as Cas touched him.

**Notes for the Chapter:**

> "The Taste" is a three line poem by Jack Kerouac that describes the powerful simplicity of rain.  
> I know I don't have much published, and maybe it sucks right now. My AO3 account is new, so I'm still trying to figure out how to navigate this side of the site. Bear with me. I'll try to update regularly, and I've already written a few chapters. I'm not sure how long it will be yet, and I know lots of people don't like to get involved in unfinished works (me included. Oops.) But I would really appreciate feedback, criticism, whatever you have to throw at me that could help improve this fanfic.  
> Thanks :)  
> Side note, I used to live in Kansas. The descriptions of places and weather is mainly from my memory and experience. Especially the weather *shudders and sips coffee from the cooler mountains of Washington, remembering the days of muggy hell*


	3. The Only Truth is Music

**Summary for the Chapter:**

> Don't worry, Jo and Dean are not going to date. I'm treating their friendship as if they were brother and sister.  
> ~~~  
> It's Dean's sixteenth birthday, and his dad has a surprise for him.

2006  
16 years old  
Dean caught the keys with his right hand, closing a fist around the metal and relishing in the jingle. His head snapped up in disbelief and met his dad's smiling eyes.

"How you feel bout taking her out for a drive? You know, now that you got your license and all."

Dean sputtered for a couple seconds before straitening himself and nodding vigorously. "Yes, sir. Thank you. I'll take amazing care of her."

John's features crossed into a serious expression, although Dean could still detect the amusement in his eyes. "You better, or I'll have your head."

The sixteen year old allowed his mouth to slide into a thrilled grin, and he tossed the keys in the air before grabbing his leather jacket on his way out the door. 

"Oh, and Dean?" John stopped him, "Happy Birthday."

As he was jogging out the door, mind occupied with the anticipation of legally driving Baby, he ran smack into a human body that grunted out a, "Watch where you're going, boy."

Dean's head snapped up in surprise. "Bobby!"

The surly man rolled his eyes and patted Dean on the shoulder. "That's my name. Where you off to in such a hurry?" 

Dean took advantage of the conversation to slide his jacket on. While there was no snow—or ice, thankfully—it was still January. Consequently, it was fuckin cold. Midwest winters could be brutal even without the inches of snow piling on and the days long ice storms that shut down whole blocks and had families resorting to good old wood fires and sleeping bags in the living room. 

He held up the loaned keys from his father to show his surrogate uncle, earning a whistle from the older man. "Better bring her back without a scratch or your dad'll skin ya. That'd be a real downer on your birthday. How old are you anyway? Sixteen? God damn, quit growin'."

Bobby let him go on and Dean walked over to the adjacent garage, barely restraining himself from sprinting. There was no feeling quite like the purr of the Impala's engine that roared when he pressed on the gas pedal, the crashing and growling of classic rock a necessary accompaniment. The '67 Chevy Impala was a graceful beast, an extension of John Winchester himself. Sometimes it seemed as if the two of them were one, and Dean would wonder where his father stopped and the car began. When he was younger, he'd hug his dad excitedly at the end of the work day, and he'd smell the same distinct scent of leather and aftershave that perforated the inside of the Impala. The house, on the other hand, belonged to Mary. She was everywhere: in the warm, freshly baked pies, in the lavender laundry detergent that clung to all their clothes, in the melting candles she'd light constantly. 

Even though she wasn't technically his, Dean always looked forward to the moments John would relent and give his son the wheel, if only for a little while.

The door to the Impala creaked familiarly as Dean pulled it open, and he slid into the car, ducking his head under the low top. He turned the key in the ignition after a moment's hesitation, excitement humming as the black beauty roared to life under his hands. He ran his fingers over the shiny leather of the seats, trailing them across the steering wheel and over to the tape deck. Grateful for his shared taste in music with John, Dean reached for the box of cassette tapes, rummaging through before he found his favorite Zeppelin album. The smooth classic rock poured out of the Impala's speakers, and Dean sang along as the chorus for "Ramble On" picked up, tapping his fingers to the new intensity. 

"Ramble On, and now's the time, the time is now, to sing my song."

The rumble died down to a low growl, and Dean backed her out of the garage, careful not to scrape her sides on anything.

He tore out of the driveway, tires squealing as he floored it to the end of the street and whipped around the corner. Baby purred, engine revving as she flew by frostbitten lawns, neighbors leading their dogs outside for a morning pee, withering flower beds struggling to make it through the unforgiving winter, and idiotic squirrels testing death as they darted out in front of the fast moving car. He completed the full circle of his block as he turned onto his street.  
Next step: Cas's house. No way he was doing this without his best friend. Dean let the car idle on the wrong side of the curb by Castiel's house and revved the engine a few times. After he honked the horn, a disheveled bed head peaked out the front door, looking ready to tear somebody a new one when he saw Dean.

"Heya Cas. Get in the car."

Cas meandered out of his house cautiously, eyeing the car with trepidation. "I'm not getting in that thing with you."

"Aw come on. She won't bite," Dean drawled.

Cas continued to stare warily before giving in and walking around to the passenger door. "Only because it's you're birthday and you've reached a 'milestone age.'Just so you know, if we die, I'll kill you."

Dean threw back his head and laughed. "And if I mess up the impala, my dad will kill me. I guess I'll be dying multiple times."

He shifted the stick to drive and peeled away from the safety of the curb. Cas clung to the door handle, the edge of the seat, even Dean at one point. Anything to tether him to something solid while his best friend drove like a maniac. "Ramble On" had been put on repeat, and Dean's rough singing voice covered Zeppelin's. The joy was evident in his eyes and his smile as he invested his being into the lyrics.

"Mine's a tale that can't be told, my freedom I hold dear."

Cas hummed along to the music, content as usual to just listen to Dean's voice. After a while though, Dean seemed to calm down, the initial thrill having receded and been replaced with a simple awe for the car and her movements. He drove her smoother, gliding down the miles of empty Kansas interstate with Cas by his side and the roar of the Impala's engine beneath him. If the weather wasn't so damn cold, he'd roll down the windows and taste the landscape as it passed by.

Cas watched out his window as the barren fields passed in a blur. If he concentrated enough, focused his sight on a patch of earth, it would freeze, standing still in time while the rest of the world tumbled fast beyond it. Of course, Cas knew the land wasn't moving. It was them. Still, sometimes it seemed as if the world kept spinning faster and faster, not stalling for two insignificant teenagers in a vastly flat, landlocked state. And so, their only choices were to cling to each other while the rest of life hurtled on, or they could give in to the tidal wave and hope they weren't torn apart.

"Hey Cas, buddy. You're pretty quiet over there."

Cad shook himself out of his chaotic thoughts and turned to smile at Dean. "I'm just thinking about tidal waves."

Dean raised an eyebrow. "You wanna be an oceanographer or something now?"

"No, I mean how life seems like a tidal wave. Always pushing and pulling us along even when we don't want to leave a moment in time. But we don't have a choice, really. We can't linger forever."

The other boy was silent, as if trying to digest Cas's contemplating thought of the day. Finally, he settled for, "We should go get some burgers."

Despite Cas's protesting that seven a.m. was too early for burgers, Dean paved right over all his complaints by the simple argument that it was his birthday. And he wanted a fat, juicy, bacon cheeseburger.

So the two of them pulled into Harvelle's Roadhouse, the local bar and burger joint owned by none other than the Harvelles. Shoulders hunched against the biting wind, the friends breathed sighs of relief when they were enveloped by the welcoming warmth of the inside.

The only occupants at the moment were Mr. Jenkins, aged member of the Lawrence community and Roadhouse regular, and Ash, the brilliant techie who went to college when he felt like it and could easily land a job at Microsoft if he tried. Sometimes it looked as if like he'd moved himself into the Harvelle family because he was around so often. All for the better though, Dean thought. Jo and Ellen had suffered greatly when Bill, father and husband of the family, died in a hunting accident, and the presence of Ash seemed to bring some semblance of comfort. 

Also, he was Dean's ticket to alcohol if the twenty one year old was feeling generous. At the moment, Ash was sprawled lazily across a booth, mullet swept behind his shoulders. He held a beer can in one hand and tapped away at his laptop with the other. Five o'clock somewhere.

He glanced up momentarily when the bell announcing their entrance rang, offering a nod in greeting, before refocusing on whatever it was he was up to.

"Dean! Cas! 

They turned to see Jo leaving the kitchen, a bright smile on her face and towel in hand. "Nice of you to stop by. We're a bit slow this morning."

"Then how come you're up? Your wake up time usually isn't for another few hours."

Jo rolled her eyes. "I think mom's pissed at me again. This is her payback: making me work when there's no need. I've already had two cups of coffee. Anymore and it'll have the opposite effect."

"Why is your mother angry?" Cas asked, concerned. 

"Oh, you know Ellen. I could put the towel back on the rack wrong and she'd have me mopping floors."

"I heard that, Joanna Beth!" Ellen's raspy voice shouted from beyond the kitchen doors.

Dean cringed, not wanting to bring on Mrs. Harvelle's wrath. "So . . . does that mean we can't steal you away for a ride in the Impala?"

Her eyes widened. "No . . . You—really?"

He held up the keys as proof, and Jo leaned against the bar counter with a low whistle. "I'll be damned, Winchester. How'd you manage that?"

"I have no clue. He just threw me the keys this morning, told me to take her for a spin, and said happy birthday. Didn't say much else."

The blonde shook her head in disbelief. "Wow. Well, I can't sneak away, but I can bring you some food. What'll it be?"

Dean rattled off his usual while Cas flipped thoughtfully through the menu. It didn't matter that they visited the Roadhouse on a daily basis—Cas still insisted on reading through the choices before making his decision. After deliberating between a barbecue burger and plain old American style cheeseburger, Cas ordered the classic with orange juice (his attempt to make it into breakfast.)

They settled into a booth, the stillness wearing down on Castiel and causing his eyes to droop. Dean was trying to decide whether to leave him alone or squirt ketchup on his face when Jo set two plates down onto the table and slid in next to Cas. Despite her earlier misgivings, Jo had poured herself a third cup of coffee and was sipping it periodically.

Dean sank his teeth into his burger and moaned loudly when he discovered that the taste once again exceeded his expectations. He chewed noisily for a bit before noticing Cas and Jo staring at him. "What?" He asked, the words muffled and distorted behind a wad of meat and buns.  
"Why must you do that?" Castiel asked.

"Do what?" Dean mumbled around the food in his mouth.

"That," Jo nodded at his table manners. Or lack thereof.

Dean swallowed. "I'm just enjoying a delicious burger."

"It's disgusting," Cas insisted. 

Dean rolled his eyes and reached for Cas's orange juice to wash down the bite, ignoring his friends petulant protests. As he finished drinking, he found his eyes drawn to Jo as she adjusted her shirt. He didn't mean to, but he still stared at her chest peeking out above her undershirt. 

Somehow, between junior high and high school, Jo had changed from a lanky little girl, all elbows and knees, into a budding woman. Immediately he recoiled from the thought, creeped out at himself to even be thinking about it. Jo was practically his sister. In another life he'd be Dean Smith with an annoying but tough younger sister, Jo Smith.  
But he still found it weird that the girls around them had grown up without warning.

All the while, Dean and Cas were still stranded in that awkward strip on the timeline from boy to adult. 

 

Cas had caught Dean looking down Jo's shirt, and was beyond thankful she was too tired to notice. The jealousy that flared up inside him was so sudden and so violent that he almost dropped his orange juice. This was ridiculous. Dean was free to pursue any girl he wanted.

Well, except probably Jo. She might rip out his throat if he tried.

**Notes for the Chapter:**

> The purpose of chapters 1 [prologue], 2, and 3 (possibly 4) are just to set up the background to Dean and Cas's friendship. Most of the story will take place their senior year/summer.


	4. My Witness Is the Empty Sky

**Summary for the Chapter:**

> Dean is just being unfairly sexy.  
> Also, the sky is pretty.

2007  
17 years old  
Summer before senior year  
______________________

Cas leaned against the fence that separated the yards, watching as Dean hovered over the Impala's engine in an attempt to "show Sam the ropes" so to speak. The mid July day was scorching as usual, the cloudless sky glaring down on them. Breezes were fairy tales at this time of year, fables whispered to children as they melted outdoors. The trees were useless, their leaves green and alive and mocking, their shade offering no reprieve from the thick, muggy air. Winter and summer were polarized, a dry, deathly cold pitted against a wet, scorching heat.

With that summer heat came salty sweat that collected at your hair follicles and dripped down your face, stinging your eyes and slicking up your neck. Deodorant was practical in name, useless in practice. When fresh sweat dampened your armpit every five minutes, deodorant wasn't good for much other than a few short lived minutes of self confidence. 

On the other hand, sweat caused shirts to cling to skin and muscle.

Dean pointed out different parts under the hood, explaining the individual workings to his little brother. Sam, while he didn't seem much interested in the organs of the car, was drinking up his older brother's attention. Cas always found Sam's admiration for the elder Winchester rather endearing. He too only had one younger sibling, but Anna was fiercely independent. She often tried to boss Castiel around and, when they were younger, pretended to be a warrior angel in charge of a garrison. She, naturally, was his superior. Gabriel would refuse to play along, insisting that since Gabriel was the name of an archangel, he was superior to all of them. Since Michael could utilize the same argument, and Luc just sulked around, Cas was stuck playing games with the baby of the family.

Dean was adding more antifreeze or coolant to the radiator while explaining the importance of not letting the car overheat because then it would blow a gasket. Sam leaned against the bumper as Dean talked about how the mixing of the oil and water would ruin the engine. As he explained overheating, he took his greased hands out of the car to tug his shirt over his head. Subsequently, Cas's breath stuttered. Dean tossed the sweaty t-shirt to the side before resuming his lesson. Cas half wanted to go over there and take Sam's place.

Dean shifted, back muscles flexing as he moved his arms around the inside of "baby." Stupid, lucky car.

He wanted to slap himself then for being jealous of a car.

Cas's mind was at war with himself; part of his brain fought valiantly to tear his attention away from the gloriously slick, freckled back of his best friend, while the other 99% percent laser focused on those thick, rolling, beefy—

"Cas!"

Dean's call startled Castiel from his internal turmoil. He realized soon after with searing embarrassment that Dean had probably caught him staring. Does he apologize? Pretend he was staring at the car? Rub the knotted muscle in dean's right upper back?

Cas shook himself after finding his mind had wandered once again.

"Uh, yeah?" he managed to get out of his mouth.

Dean grinned, one hand gripping the lid of the trunk, the other resting against his jeans. "Wanna take a peak at her? Most people don't get to see her all...open and exposed like this." Dean wiggled his eyebrows suggestively. Sam just rolled his eyes.

"Dude, how many times do we have to remind you? It's a car, not a pornstar."

"She!" Dean looked affronted and rubbed his car with affection. "Don't listen to him, baby. You'd look great in a porno."

"Hey, Cas, could we have those cokes?" Sam asked, ignoring his brother.

Cokes. Right, the cokes. The cokes Cas had been sent inside for in the beginning. The cokes for Sam. And Dean. He somehow managed to get his legs working enough to make his way over to Dean, forcing down unwanted feelings, and offered a cold drink to each brother. "Thought you mind want some refreshments."

"Thanks, Cas," Sam said with genuine gratitude.

"I, uh, also made sandwiches if you want."

"Dude," Dean said after he took the coke, pointing at Cas with his free hand, "You're awesome."

Cas smiled easily and started to reply when Dean wrapped his lips around the mouth of the coca-cola bottle and tilted his head back. Consequently, all rational thought fled Cas's mind.

Cas watched, rapt, as his friend swallowed greedily, throat moving and adams apple bobbing as the coke made its way down his throat. His fingers formed a firm grip on the bottle, and the condensation dripped down his fingers, trailing over his arms and marking paths in the dark patches of grease.  
He pulled his mouth off the bottle with an audible pop, and licked up the neck of the bottle to catch a stray drop of soda that ran down the side. He licked over his lips to gather up any excess liquid, and Cas wondered with despair why he had to drink so fucking provocatively.

Cas backed away a few steps, tried to ignore his stiffening cock, and mumbled something about getting the sandwiches.

He barely restrained himself from running into his house. Once he was safely inside, he leaned against the wall in relief and brought up images of old, wrinkly grandmas in bikinis. His nose scrunched up in disgust, and he vowed to take a cold shower next time in order to avoid such unpleasant images.

It worked, though, and he felt his pants loosen slightly. Cas made his way into the kitchen to grab the wrapped up sandwiches. Before leaving, he picked up a soda for himself and made his way outside.

Thankfully, Dean had made use of his shirt again, and Cas could breathe a little easier. Dean closed the lid of the impala and he and Sam sat lightly on the edge, watching the light gradually fade as sunset approached.

Cas held up the plate of sandwiches like a peace offering before taking his place beside Dean. The three of them unwrapped the food in silence as they watched the colors paint the sky. Cas would never get used to the magnificence of Kansas sunsets: with a flat landscape and scarce trees, the open sky dominated the scenery. He loved being able to look up and be met with an immeasurable expanse of blue during the day. The sky was the sea of the midwest, as beautiful and unpredictable as the oceans of the coast. As a kid he used to toss his head back when he pumped his legs on the swings, tossing his head back so that the world flipped upside down. It made him feel like he was flying on a far away planet where the sky stretched beneath his feet and he waded through the clouds while the grass grew above his head, a textured green blanket.

Today, the sun bled red and orange as if it were a wounded soldier sinking below the trench that was the horizon. Streaks of scarlet ran across the darkening sky, painting the death scene of the star in dramatic color.

At least until it would rise again in the morning, unscathed, bathed in brilliant white light and haloed with pale pink and soft morning glow.

Their sandwiches finished, the boys followed the sun's descent into darkness, not leaving the car until the stars crept out for the night.

"Alright, what do we give it?" Dean asked, throwing his head back to catch the last of the drops of pop.

"Ten," Sam answered after a moment's thought.

"What he said," Dean clanked his bottle against his brother's.

"I'm going for an eight," Cas decided. He'd never rated a sunset a ten before—he kept waiting for one that would blow his mind.

"You going to go to the grave on sevens and eights?" Dean asked, eyebrow raised.

"I'm just waiting for a sunset brilliant enough to warrant a ten."

"Uh huh, so you've said. We'll crack him one day, huh Sammy?" Dean ruffled his brother's hair with affection.

"It's Sam," the younger boy grumbled, but it was half hearted. 

~~~~~~~~

 

Cas didn't feel like dealing with his family that night, so Dean let him sleep over. 

"I gotta shower though, man. I'm disgusting."

Not from where I'm looking.

"Whatever you need to do. I'll just watch some tv."

Dean disappeared into the bathroom he shared with Sam, and Cas flipped on the old television Dean had sitting on a dresser in his room. The static cleared to reveal Game of Thrones, a shared favorite show between Cas and Dean. Although there were times Cas suspected Dean only watched for the nudity. He personally enjoyed the complex story lines entwined and knotted together in clashes of knights and weddings and betrayals and plotting. 

He followed the story arcs of the Lannisters, Starks, Baratheons, Greyjoys, and Daenerys with interest, and found that he remained unaroused during the intimate scenes. It was in the middle of a conversation in Littlefinger's brothel that Dean emerged from the bathroom, wet hair tousled and chest dripping wet. He'd wrapped a towel around his waist that hung low on his hips, and Cas swallowed hard. Maybe now he was a bit aroused.

He sent frantic messages down to his dick that went unreceived, so if Dean noticed he would have to blame it on the television.

"Sorry, man. Forgot to bring clean clothes." He flashed a winning smile that Cas shakily returned, carefully moving a pillow over his lap when Dean turned to his dresser to rifle through the drawers for something to wear.

Cas struggled valiantly to keep his eyes on the two nude females on the tv screen, but it was as if Dean was a magnet and Cas's head had been replaced with a metal ball. Soon, the volume of the feminine moaning on the screen caused Dean to turn back around, clothes in hand and eyebrows raised. 

His towel had slipped even further and Cas pressed the pillow down harder, biting his lip against the groan that tried to escape at the friction. Bad idea then. Dean gave Cas a strange look.

"You okay dude?"

Of course Cas's natural reaction to being put on the spotlight was to blush furiously. Dean furrowed his eyebrows at him before glancing at the pillow, then to the tv screen, then Cas's uncomfortable expression, then back and forth before he burst out laughing, clutching at his towel to keep it up while he bent over. The reaction did nothing to fade the fire in Castiel's cheeks, and he squirmed on the bed.

Dean let out a few more laughs in between deep breaths before leaning against the wall and sighing. "Thanks for that. I needed a good laugh."

"I-I didn't mean," Cas stammered.

"Bathroom's all yours if you need it," Dean offered, amusement in his eyes. 

"Uh, no, no. I'll manage."

Dean rolled his eyes. "Whatever you say. Hey, wanna go up on the roof tonight?"

"Go get changed. I'll grab the blankets," Cas instructed, glad for a topic change. Once Dean had left the room, Castiel breathed a sign of relief and cursed his overexcited cock. That was twice in one day. Twice. If he couldn't get things under control, hanging out with his best friend would prove to be painstakingly awkward. 

He busied himself gathering blankets and sliding open the window that led to a small ledge that provided a step onto the shingled roof. Cas climbed carefully over to the peak of the roof next the the chimney where he laid out the blanket. 

Dean's head appeared over the roof and he spotted Cas already lying down on the picnic blanket. He joined his friend, trying to get comfortable on the hard surface.

"I found Scorpius. To the south," Cas informed Dean, pointing in the direction of the Milky Way. 

"I think that's Sagittarius right next to it," Dean said, head tilted to the sky.

"The Scorpion and the Archer."

They spent a few minutes pointing out other constellations spread throughout the Milky Way, Cas rattling off scientific names and their backgrounds and Dean listening with interest. Castiel had a multitude of random facts, tidbits, legends, and information stored in his brain that never failed to fascinate Dean.

After a lull in the conversation, Dean broke the silence. 

"What would you do if the sun never rose again?"

Cas let his head fall to the side to look at his friend. "What do you mean?"

"We take for granted that the sun will rise at six or six thirty or whatever the hell time it does its business. But what if one day, it didn't? What if the darkness just stayed? And the world ended? What would you do?"

I would kiss you, Cas thought. But he couldn't say it out loud. Not now, not ever. Those were the things you saved for if the world really was ending. And while Castiel wouldn't be surprised if his own siblings managed to bring on the apocalypse, the reality was that his deepest desires and dreams would stay in the darkness forever. 

So instead he told Dean, "I imagine I'd just sit here quietly."

Dean propped himself up on his forearm, staring down at Cas in disbelief. "Seriously, dude? I mean, no girls, no booze? Not even pork rinds?"

That earned a half smile from Castiel who was currently holding his breath at having Dean leaning so close to him. "Well, I suppose I'd make an exception for pork rinds." He waited for Dean to add something, but the other teen just rolled onto his back again.

"What about you?"

"Huh?"

"What would you do if the world ended tomorrow morning? You never answered your own question," Cas reminded him.

"Well, it'd be awesome to go out with a bang, if you know what I mean," Cas rolled his eyes at that, "But, god this sounds like a chick flick moment, I'd rather spend it with you."

Cas smiled, knowing that a response would probably embarrass his best friend. But his brain went insane with the information, wondering what exactly Dean meant by that statement and generally being a nuisance. 

If Cas was brave, he'd grab Dean's hand and squeeze it.

But he hadn't worked up that courage. And he likely never would.

**Notes for the Chapter:**

> Please let me know what you think so far in the comments and if there's any direction you'd like the story to go in.


	5. Climb That Goddamn Mountain

**Summary for the Chapter:**

> It's hot. There are half naked bodies and ice cubes.  
> But on a more serious note, Cas is having some major inner turmoil issues.
> 
> This hasn't been reviewed, so I apologize in advance for any stylistic or spelling/grammar errors. Feel free to correct me.

The following day brought another round of the heat wave that was Midwest summers. Pools were crammed to full capacity, water and air conditioning bills skyrocketed, and small children tried to crawl inside their fridges. Or maybe that was just Sam, who was definitely not a small child by size at least. He was scrawny, but his gangly limbs and large feet predicted tallness in his future. For now, though, he was just a nervous little fourteen year old trying to enjoy the summer before the anxiety and nerves over starting high school kicked in.

John had left already to go work at the auto yard he co-owned with Bobby Singer. Mary would normally be at home—being employed as a teacher was rewarding in that she got to spend summer vacation with her boys—but that weekend she was away on a seminar for the AP English class she taught.

Consequently, Dean and Sam were left to find things to do at home since John had taken the car to work instead of his newer pickup to repair some internal problems. They were both plastered to the couch, mindlessly flipping through channels while no less than five fans blasted room temperature air at their faces. They'd both already removed their shirts, and if Dean was alone he probably would have been naked at this point.

"I just don't understand why our air conditioner always has to break," Sam whined and pressed a cold pack to his face.

"You know those are for food, right?" Dean asked.

Sam just glared at him, flashing his trademark bitch face. "Jerk." "Bitch." The bickering just intensified with the heat. 

The new hour brought paid programming to their TV, although Dean wasn't sure why infomercials would be on at three in the afternoon. They watched in jealousy and dismay as an overly cheerful man in a suit and tie advertised the benefits of his "new and improved" window air conditioning unit. If he was able to wear a suit, then the damn thing must work well. Dean sighed, about ready to intrude on Cas's family to take advantage of their cooler air when the doorbell rang.

Sam didn't remove his eyes from the TV, a silent passing of the responsibility of answering the door to Dean. With over exaggerated groaning, Dean heaved himself up off of the couch and lumbered over to the front door. A quick peek through the window revealed a sweating Cas.

"Cas! Man, I'm so glad you're here. We're melting in this hell hole. Mind if we crash in your basement?" 

At Cas's apologetic expression, Dean felt his hopes sink. "Ah, no. Not you too."

His friend just nodded morosely. "I'm starting to think this block is cursed."

"Well, if your house is toast too, what makes ours any better?" Dean asked.

Cas just shrugged. "I'd rather just be hot than bored and hot."

"Fair enough," Dean nodded and waved his friend inside. He took one look at Sam, who'd managed to wave an arm in greeting and currently seemed to be one with the couch, and decided they'd head somewhere else.

"Let's just go to my room," Dean suggested. It was arguably one of the coolest rooms in the house, besides the basement. And Dean didn't really want to spend the next few hours cramped in a cement tornado shelter among shelf after shelf of canned goods. They entered Dean's room and Cas collapsed on his bed after removing his shirt.

"Well, Cas, I'm awfully flattered, but I don't think that activity is a good idea in this heat."

Cas huffed, and a Dean could picture him rolling his eyes. "It's hot as hell, Dean. I'm gonna wear as little clothing as possible."

You're gonna get my sheets all sweaty," Dean complained.

"And you're not?" Cas mumbled from his prone position.

A lightbulb went off. "I have an idea!" Before Cas could respond, Dean dashed down the stairs into the cellar where the deep freeze rested. He hauled out a jumbo bag of ice and pressed it against his body, relishing in the cold, before taking it back upstairs.

Cas didn't look up when Dean returned, and so formed a mischievous but ultimately fun plan in Dean's head. He sat on the bed beside his best friend and reached into the stuffed ice bag. Carefully, quietly, he pulled out a handful of ice cubes and plopped them down on Cas's back. 

Cas yelped and arched his body off the bed. "What the hell, Dean?"

Dean chuckled at his reaction. "Just trying to cool you off." When Cas didn't protest, Dean grabbed another few cubes and placed them on his back, rubbing them around while they melted. 

"I'll do you and you do me?" Dean suggested.

Cas lifted his head off the bed enough to raised both eyebrows at Dean. His face was bright red, but it was ninety plus degrees in there.

"Shut up."

"I didn't say anything," Cas retorted.

Dean just responded by replacing the now melted ice cubes with a fresh batch, causing Cas to jump. He grinned and rubbed the ice up and down his friend's back, from his neck all the way to the top of his shorts. The more ice he rubbed in, the more he noticed how tense Cas was.

"Dude, your back is in knots."

Cas just shrugged as best he could. Dean made a decision then and swung his left leg over Cas's body so that he was straddling his back thighs. Cas stiffened in surprise and started to protest before Dean shut him up. "Calm down, I'm just gonna work out the kinks." 

He worked the ice into his massage, kneading his fingers into the trapezius muscles while the ice stayed trapped under the palm of his hand. Cas seems to relax slightly at the massage, and Dean took that as encouragement to press harder and deeper as he tried to roll out Cas's stiff muscles. He continued to move further down his friend's back, palms pushing into Cas's lower back.

Meanwhile, Cas bit his lip so hard he feared he would draw blood. The way his body was reacting to a fucking massage was absolutely infuriating. He was forever grateful to be on his stomach—otherwise he would never have been able to hide the fact that he was hard. He was afraid to even shift his hips, knowing the friction would either rip a moan out or force him to stay on his stomach until Dean left the room for some reason. 

He tried to relax, knowing that Dean might think he was uncomfortable and stop if Cas remained tense. Because despite the fact that he was turned on by his best friend and things could get rather awkward pretty fast, Cas really did not want Dean to stop.

So he sucked it up best he could and managed to curl his hands loosely at his sides rather than fisting them in the sheets. Dean's thighs were pressed against the outside of Cas's hips, his knees brushing closer to his waist. The heat from the contact coupled with the warmth of the room cancelled out all of Dean's attempts to cool his friend down.

He could feel the sweat rolling down his back and pooling in the divot of his spine. Or maybe that was the water from the melted ice. 

Suddenly, Dean swung off him, and Cas didn't know whether he should be relieved or disappointed. But Dean plopped onto his back and lifted his arms to grab his bed posts and stretch, pulling his abdomen muscles tight and deepening the hollows at his hips. 

Cas swallowed.

"My turn," Dean grinned.

Cas tried to still his rapid beating heart, ignore his erection, and find his voice all at once. Clearing his throat, he managed to get out a joke, "Your pits smell like hell."

Dean cracked open an eye. "Then don't smell them."

Cas shook his head at the Winchester's logic. "Go ahead and get started. I have to. . .urinate."

The bark of laughter from Dean's mouth startled Cas. "Dude, that was the weirdest sentence ever. You can't mix sexy talk with body functions."

Cas scrunched up his face. "I wasn't—"

Dean waved him on. "Nevermind," his face was flushed and his eyes were smiling, "Go take a piss."

Cas locked the hall bathroom door behind him and leaned heavily onto the counter. As much as he wished his sexual thoughts would leave for good, he couldn't help but be confused by Dean's actions. For a man who professed his love for girls on almost a daily basis—which shouldn't bother Cas—he sure seemed to flirt with guys. Or maybe Cas was just reading into it because of his own biased hopes. 

But still, he couldn't help but recall the time Dean had ran into a fucking table, obviously flustered, when he realized an older guy, possibly college aged, was flirting with him. Cas had watched the exchange with interest, surprised at how long it took Dean to realize what was happening. The two of them had gone to the Roadhouse to eat dinner after a long day of practicing lacrosse, and the older student had slid into the booth with Dean while Cas went to the bathroom. 

Dean, with or without realizing it, had been encouraging Aaron's advances. His body language—easy smiles, winks, and lip biting—had sure seemed to Cas like a returned interest. Apparently, Aaron had thought so too. When he slid his number across the table to Dean, the younger boy seemed visibly shaken.

"I, uh, I'm not," he fumbled for the words while Aaron watched with a mixture of confusion and amusement. Before Dean got the chance to tumble over a chair, Cas stepped in and put a hand on his friend's shoulder to steady him. 

Understanding passed over Aaron's face. "I'm sorry, I didn't realize you already had someone." Dean started to protest, but Aaron fixed his gaze on Castiel. "Lucky guy."

With that, he'd walked off, leaving Dean gaping after him.

"Dean," Cas had began.

"It's nothing, Cas. Are you ready to go?"

The gruff, clipped demeanor that Dean had undertaken after the encounter hit Cas hard. Dean was obviously disgusted by homosexuality, or at least uncomfortable around it. Unfortunately, that revelation did nothing to squelch Cas's developing feelings.

Two years later, Cas was still struggling with deciphering Dean's feelings towards the topic. He'd remained terrified to ask, knowing he may hate the answer.

Cas couldn't even come out to Dean as gay or bisexual because he didn't know what he was. He'd never really been seriously attracted to anyone other than Dean, which was a terrifying truth.

Looking down, he breathed a sigh of relief to discover that his hard on had softened enough to where it wasn't visible. He quickly flushed the toilet and scrubbed his hands to keep up appearances and exited the bathroom. 

The return to Dean's room almost sent him back, though. 

So much naked skin. Cas said a prayer to whoever was listening and thanked them for hot summers existing. 

Dean must have heard him come in because he opened his eyes and propped himself up on his elbows. "About time. I'm melting over here."

Me too.

"I mean, we could always practice lacrosse, but that doesn't start for several months so . . ." Dean trailed off and smiled lazily. Several months. It hit Cas then that he was one short month of summer away from beginning his senior year of high school. His last season of lacrosse. 

The sport had captured Cas's interest freshman year, but he was afraid of not making the team. Dean had proceeded to spend the rest of the summer (and some of the school year) attempting to convince Castiel to try out for the team. Apparently, all his persuasion had piqued his own interest, and Dean had accompanied his friend to tryouts. Cas quickly discovered that all his pent up frustration translated well onto the field. He played with a determined viciousness that quickly helped him climb the ranks. Dean too played the game with deadly precision, and Cas always felt sorry for whichever team they played against. The Angels of the Lawrence High School lacrosse team never failed to prove themselves as fearsome warriors rather than peaceful harp players. 

However, for all their bravado and skill on the field, they were still evenly matched with their rivals at Roosevelt High, the devils. Last season, the Angels had won the district championship, cutting the Devils out of the running for the regional championships. The Angels, while they played admirably, failed to take the regionals title home. But this upcoming season offered a chance to take the district trophy for the second year in a row, and Cas was looking forward in constant anticipation. Sometimes, he felt as though time spent not practicing was worthless.

Unless he got to spend time with Dean.

Cas leaned against the door frame and eyed his best friend. "I don't know, Dean. It's our senior year. We can't really afford laziness."

Dean just groaned and fell back onto the bed. "I can damn well afford it right now. We go out there to practice in this hell, we'll die of heat."

"You're afraid of swooning from the heat?" Cas teased. "If we can't endure this Hell on earth, then we've already lost to the Devils."

"Cas," Dean whined. "You're being dramatic." His eyes were closed again, one arm thrown across his face, the other resting at his side. Silently, Castiel reached into the bag of ice and drew out a handful quickly. Before Dean could remove his hand to investigate, Cas slammed his hand down onto Dean's abdomen.

His best friend yelped in surprise, stomach muscles tensing. Cas just grinned wickedly. "'Just trying to cool you off,'" he threw Dean's earlier words back at him.  
His light banter couldn't distract him forever from the fact that his hands were on Dean's chest. Cas knew they touched more than most guy friends—whether it was the frequent hugs, arm brushes, or simple close proximity, Dean and he had always been physically close. It'd never bothered him, or Dean from what he could tell, but he remembered the jabs and jokes that were thrown at them in middle school. He remembered the day he first learned the word fag, how he curiously asked his older brother Gabe what the word meant.

Gabe looked momentarily sad, said he wished Cas never had to hear the word. But, nevertheless, he told him that he would probably hear it again. And the only advice he gave his little brother was to not let it bother him. The people who said it were ignorant, they were mean. They were people Cas didn't want to associate with. 

And, more importantly, he said to be patient with Dean.

Cas hadn't understood it at the time, hadn't really thought about the fact that his and Dean's friendship was slightly different than other boys. He wasn't ashamed of the fact that he wasn't afraid to show affection, but he later realized that Dean might be. 

The remarks didn't disappear, but they dissipated somewhat. Or at least, they did for Dean. Once he'd established himself as a hotblooded American male, his couldn't care less attitude and pursuit of women earned him a bit of a reputation. Dean had really flourished in high school.

Cas, on the other hand, was more of a freak. He'd never had a girlfriend to anyone's knowledge, he was awkward around people he didn't know very well, and he rarely spoke. Dean had no idea about the threats Cas had received, the disgusted remarks spat at him in deserted locker rooms and behind the school building. Dean had no idea because Cas didn't tell him. Cas knew his friend, and he knew Dean's volatile temperament would only make the situation worse. 

So, he kept silent all the years, content to have friends and teammates who never judged him and to just ignore the others.

Unfortunately, try as he may, he couldn't ignore his hormones or his traitorous mind as he rubbed the ice over Dean's body. Thankfully, his friend had closed his eyes again. Cas didn't think he could successfully complete his task if he knew those green eyes were watching him. And so he fixed his gaze on summer tanned skin, devoting his hands to the job of tracking ice over flesh.

He was quickly absorbed in the sight of his long fingers trailing over the various bumps and ridges of Dean's torso. He tracked the motion, following the path of his hand from the divot between Dean's pectorals, down the center of his abdomen, fingers spreading out to catch the ridges of each ab muscle like rolling hills on a plain. Dean didn't have washboard abs—his stomach was soft in many areas. But Cas found that fact all the more fascinating as he pressed the ice into the skin around Dean's belly button. He paused at the hairless skin above the waistband of Dean's shorts, intently focused on that barrier. 

"Cas."

Dean's strained voice startled Cas's relaxed thoughts, and he realized with abject horror that the ice had already melted.  
His hands were just resting between Dean's hipbones, pinky finger a hair's width away from the rippled band at the top of the shorts.

What was even worse, he couldn't move his body. He desperately needed to remove his hand, but he simply couldn't make the signal travel from his brain to the nerve endings in his fingers. Move! He screamed at his hand. But it just sat there, resting a few inches away from Dean's crotch. 

Then his eyes rolled back up Dean's torso slowly until they met hooded green eyes. He didn't know what to make of the situation, he didn't know what to make of anything. All he knew was that Dean's face was red and his lips were parted and he wasn't moving and wait. Cas's body had moved without his permission and somewhere in the back of his clouded mind he frantically tried to pull back. 

He was still leaning closer to Dean's face when the door swung open and Cas sprung away from Dean. His heart was beating like a scared rabbit's and he was sure he was blushing from head to toe. 

Sam stood in the doorway, long hair plastered to his forehead with sweat, chest heaving with labored breaths. "Dad's home and needs you to start dinner while he finishes something on the car."

And just like that, the moment was broken. Sam took off down the hallway, and Cas turned to look back at Dean. He guarded his expression, horrified at how close he had come to attacking his best friend by letting his lustful feelings control him.

Dean was pulling on a shirt, face giving away nothing as well. Cas hesitated a second before asking, "Want me to stay?"

His friend shrugged, then smiled slowly. "Well, I am planning on grilling burgers . . ."

"Sold." 

They grinned at each other before Dean ducked out of the room at John's yell. Cas breathed a sigh of relief, but his shoulders sagged in disappointment. While they almost took a step forward, they were yanked back to square one. Or Cas was, at least. And he was still struggling to figure out whether or not that was a good thing.

**Notes for the Chapter:**

> I'm so sorry it took so long to post this. I couldn't figure out what my end goal for the chapter was. It's the longest chapter I believe.  
> Also, I'm going to California for a week so I'm not sure if I'll be able to post or not. But I will try!  
> Let me know what you think! Leave a comment—I don't bite.  
> ...  
> But Cas might *insert weird smirking face that I don't know how to create*


	6. The Best Teacher is Experience

**Summary for the Chapter:**

> Cas gets more than he bargained for at an end of summer party.  
> _____  
> There's a threesome in this chapter, although I didn't go into much detail. I'll explain why in the end notes.

"C'mon man, every bit of gel that goes into your hair increase your douche level," Dean complained from his bed. Gabe had let him in a few minutes ago, and the older Winchester had waltzed right into Cas's room. Castiel worried his brand new lip piercing with his teeth, wondering what his best friend would say.

So far, Dean hadn't seen Castiel's face, but he could observe his hair styling adventures from where he lounged lazily on the bed.  
Nervous, Cas continued to work his hair over, spiking up the unruly strands. His attempt at managing his "sex hair", as Dean called it, never really ended well. He was just aiming for a spiked up look as a last ditch effort to change up his appearance for senior year. Lisa Braeden's end of summer party was supposed to be pretty wild, and it seemed as good a time as any to try out something new.

Although, Cas wasn't thrilled about Dean's monster crush on the girl. Not like he had a right to be jealous or anything, but it still bothered him. From what he'd heard of Lisa, her personality was not unlike Dean's, so Cas's only consolation was that they may just hook up once and move on. God, he felt like such an ass. Cas gritted his teeth in irritation, wishing his best friend's sex life didn't affect him so much.

Rinsing his hands in the sink, Cas looked over the dark leather jacket he'd thrown over a simple black tee. He wasn't quite sure about the look, but he decided his recent affinity with leather was probably inevitable because of his time spent with Dean. Taking a deep breath, he turned to face his bedroom, fidgeting with the zipper. 

Dean sat up quickly, surprise etched onto his features. He looked Cas up and down, a move that did nothing to quell his friend's nerves. Briefly, he touched his lower lip in the spot that Cas has his lip ring. He lifted an eyebrow as he pointed at it, lips twitching into the beginnings of a smile.

Letting out his breath, Cas shrugged. "It was a spur of the moment decision."

Dean smiled all the way then. "Dude, it's awesome. Kinda badass."

And everything was okay again. Dean grabbed his own leather jacket and they headed downstairs where the Impala was waiting outside. Chuck barely spared them a glance—he was too focused on the keyboard of his old computer, cranking out a story about two brothers who battled supernatural creatures. Cas's father had published a few books, but the popularity seemed to be more of an underground cult type following. Either way, he didn't make enough to support their whole family. They had Michael for that, accomplished business man as he was. Professional and practical, he had never been the most affectionate of brothers.

As the two of them slid into the black beauty, the front door swung open, screen door banging against the side of the house. Cas turned, hand already on the door handle, before a blur of red passed him and yanked open the back door.

"What—" he started.

Anna peered at them from the backseat with wide, doe eyes framed by a wavy mane of fiery hair. She'd put on makeup, a feat she usually didn't dapple in, and a low cut white blouse exposed more than Castiel wanted to see on his sister. She threw Dean a dazzling, semi apologetic grin.

"Anna . . ." he said, warning in his tone.

"Look, Jo said I was invited. You can ask her yourself when you pick her up. I didn't mean to barge in, but I don't have a car and Jo can't take me because you're taking her," she let out in one breath.

Castiel worried his lip piercing, staring Anna down. He knew she'd hate him if he brought it up. "Look, Anna. You're not supposed to be in situations like this, remember? The doctor—"

Anna cut him off with fire in her eyes. "To hell with the doctor. I'm ready," she bit out, defiance clear in her expression that dared her brother to contradict her. 

Dean squirmed in the driver's seat, unsure of whether or not to intervene. He knew of Anna's hospitalization, of course, but it wasn't really a topic they discussed often for Anna's sake. His fingers clenched and unclenched on the steering wheel, and he caught Cas's eyes with a silent question. He was waiting for consent from Cas first.

Castiel twisted his body back around to fix his sister with a glare. "If anything happens to you, I swear to God—"

Anna rolled her eyes. "I can take care of myself. I'm not afraid of fellow teenagers and alcohol."

I'm not afraid of what they could do to you, Cas thought, I'm afraid of what you might do to yourself.

Cas hesitated a moment before nodding at Dean, knowing he would live to regret his decision. But he also didn't want to deal with the violent, bloody aftermath that would ensue if he rejected Anna.

With a turn of the key, the now three of them sped off to Jo's to rescue their blonde friend from a night shift at the Roadhouse. They rolled down all the windows, letting the summer night air flow through the cab. The nightly cool downs were a necessity after a long, scorching day. Cas knew he'd probably end up sweating too much to wear his jacket, but he wasn't ready to take it off just yet. The wind against his cheeks felt nice, and the sky was quickly darkening from a deep indigo to the inky blackness of night. 

Jo was sitting against an oak tree, blonde hair curled around her delicate face. She sprang up at the sound of the Impala's engine, however, making a beeline for the car. And if she heard the faint Joanna Beth, where do you think you're going?, she made no mention of it.

She slid in next to Anna, face lighting up. "I see you managed to convince Mr. Grumpy."

Dean barked out a laugh, and Cas just grumbled at her before realizing he was only proving her point. So he settled against the black leather with a huff, face turned towards the open window again as he unscrewed the cap on a plastic water bottle.

"So. . . any of you thinking of getting laid tonight? You know, start the year off with a bang?"

Cas choked instantly on the water at Jo's forward question. He was torn between embarrassment for himself, protection over his sister, and jealousy for whoever might end up with Dean.

He sputtered for a few more seconds before Dean reached over and clapped him on the back. "Does that mean you have someone in mind?"

Cas narrowed his eyes at his friend before shaking his head no.

"Really? Come on, man. Not even April?"

"April?" Jo piped up from the backseat, curiosity raising her voice. "I didn't know you liked April."

"I don't like April. Dean's just been trying to set me up with her since freshman year. At this point I think he should just sleep with her."

"Nah, I don't like her much."

Cas stared at him in disbelief. 

"What? Just because I'm not interested doesn't mean she wouldn't be a good fit for you."

"O-kay, can we not talk about my brother's sex or lack of sex life? I'd rather be kept in the dark, thank you very much."

Cas's cheeks lit up again.

"Alright, fine. What about you then, Dean? There's always someone," Jo directed her question at their driver.

Dean smirked, hands tightening on the wheel. Only Cas caught the smirk, and he looked away, a tightness in his chest. "Well . . ." he began.

Jo cackled. "I knew it! It's Lisa, isn't it?"

Dean's smirk grew, and Cas didn't know whether to laugh or frown at the fact that his brief wish had been answered. 

Even Anna sounded dubious. "Lisa? As in Lisa Braeden? The girl who sleeps with a different guy every week?" 

Jo wrinkled her nose. "Yeah, hope you don't catch something."

Dean came to the girl's defense. "Wow, you two are vicious. Remind me never to give you a reason to talk about me behind my back."

They exchanged a smile that made Dean groan. 

"Well, in any case, Dean would have protection of course." Cas surprised himself by not tearing her down too.

Dean coughed, which turned into a breathy laugh as he shook his head. "Damn straight, Cas."

Not exactly, Cas thought.

"I bet she's wild in bed, though," Dean said wistfully, pulling his lower lip between his teeth.

On whether or not she was wild in bed, Castiel didn't know. What he did know, however, was that she did throw insane parties. The cars lined the long driveway up to her dark house in the country, many of them parked between the trees stacked along the road. The faint bass pounded louder as they approached, and kids were spread over the lawn like ants. The house was definitely not the epicenter of the event—more likely it was a makeshift motel for those who wanted privacy and a quickie. The real attraction was the large, empty barn on her property. Her parents were apparently not interested in using the large quantity of land to raise livestock, preferring farming instead. Consequently, the barn offered a venue for raving parties. He immediately felt intimidated, but trusted Dean.

For the most part.

They found a spot further in the trees to subdue Dean's worry over his car. Cas noticed Anna's spirited demeanor had diminished slightly. She wrung her hands together, regarding the noisy house warily. Jo must have detected the signs too, because she grabbed one of Anna's hands, shooting her a reassuring smile that seemed to ebb at his sister's nervousness.

 

As they approached the barn, Dean's presence at Cas's side helped calm his own nerves. Each time they passed a scantily clad female, Dean's head rotated as if it were tied to their bodies. He decided then that before this night was over, he'd have consumed copious quantities of alcohol. 

"I don't know about you guys, but I could use a drink," Dean yelled over the loud music. Jo whooped in agreement. "Cas, wanna help?" 

Just happy to have something to do rather than stand around, Cas obliged his friend as they shoved through the thickening crowd. There were several teenagers grouped around the kegs of beer, and Cas watched in disgust as one girl knelt under the spout, tongue out as if she were going to catch snowflakes. Some guy he didn't know opened the spout to empty bear into her open lips while his friends guffawed and shoved each other. 

Although Castiel played lacrosse, he refused to consider himself a jock. He'd only gotten a letterman's jacket because Dean persuaded him too, promising it was a perfect opener to picking up chicks. And because he desperately needed Dean to not question he was into anyone other than girls.

"Just offer them your jacket," he explained. "Keep 'em warm." Dean had winked at Castiel, but all he could think about after that was associating the girls with a turkey you kept in the oven to maintain the warmth. And no girl would ever hook up with a guy who likened them to cooked foul.

Dean, taking his own advice, had shown up in his blue and white varsity jacket, boasting the pins he'd received from lacrosse. 

Even though his friend returned every suggestive smile and wink thrown his way, Cas knew he had a target in mind and that he wouldn't give up until he got Lisa Braeden in bed.

If only I could get on his radar, Cas thought foolishly.

And then Dean was shoving two Red Solos in his hand as they managed to get up to a keg that wasn't currently in use. The handle was sticky from old beer, and Cas grimaced as he stepped into a puddle of the spilled alcohol. One fumbled cigarette and this place could go down in flames. 

Once they had each filled two cups, they began the treacherous journey back out of the barn where the girls were waiting. On the way, they were ambushed by fellow team members Benny and Adam. 

The Louisianan came up behind them, grabbing both by the shoulders and causing beer to slosh out of Castiel's cups.

"Well would you look at that. Winchester and Milton. Nice of you to show up."

They turned around to greet him and found Adam by his side with that seemingly perpetual smirk. Adam was a cousin of the Winchester brothers, and he had a habit of showing up on their doorstep unannounced and uninvited. But other than being a slightly stubborn and frustrating relative, he was a pretty decent guy. Cas didn't know him very well, but Adam could definitely hold his own on the field.

Adam nodded at the drinks. "Who're those for?" he asked, wiggling his eyebrows suggestively. 

Dean just rolled his eyes. "Just Jo, dude. And Anna, Cas's sister."

Adam turned to Cas. "You're sister's here, huh? She available?"

Cas narrowed his eyes at the blonde, who got the message and raised his hands in surrender. "Sorry, dude! Wasn't even going to try it."

Benny grinned. "As if she'd sleep with you anyway, idiot."

Dean cleared his throat. "Actually, any of you guys seen Lisa around? I wanted to, you know, thank her for hosting the party . . ."  
Adam whistled, and Benny's smile widened so far Cas thought his face might split in half. "Uh huh. I'm sure she'll appreciate it."

Dean just raised his eyebrows expectantly. Benny just chuckled. "Last I saw, she was hanging around Meg outside."

Dean nodded in thanks. "Hey, I'll see you guys around. I'd hate to deal with Jo's wrath if I take a minute longer bringing her back her beer."

The other boys nodded in understanding—Jo's knife collection was well known.

"Brother, have a good night," Benny winked. Cas resisted the urge to throw up in one of the beers.

He followed Dean back outside, allowing him to steer them through the even tighter mass of people. When they finally pushed outside, Jo was leaning against an apple tree with Anna, talking to—

"Bingo," Dean breathed. 

Cas trailed helplessly after his friend as Dean made a beeline for Lisa. Jo noticed their approach and let out an over exaggerated sigh, and Cas tried not to notice the way Meg raked her eyes over his body. Meg was a Devil of Roosevelt, so Cas didn't see her much except for at games if she showed up to watch, and parties. For whatever reason, she also insisted on calling him Clarence. 

"Finally. God, what did you do, talk to every damn person in the barn?"

"Just two, actually," Cas reassured her since Dean's attention was already zeroed in on Lisa. Jo just glared at him.

Dean held out one of his beers to Lisa, the one that was supposed to be for Jo. 

"Offering me my own beer, Dean?" Lisa asked as she raised an eyebrow.

With a sheepish grin, Dean held it out to her until she accepted. 

Jo sighed, and snatched a cup from Castiel's hands. Anna followed suit, stealing Cas's beer. "Hey!" he protested. "That was mine."

He felt a warm body press against his side, and turned to look down at Meg in surprise. "Don't worry, Clarence. I got you covered." She pulled out a flask from her back pocket and offered it to him. He started to shake his head, spewing some variation of "Oh no, I couldn't," before Meg simply unscrewed the cap and tilted it into his mouth. He coughed in surprise at the intrusion before resigning himself to swallowing the warm, burning liquid. It was either that or let it dribble down his chin. 

When Meg seemed satisfied with his alcohol intake, she pulled the flask away and stuck it back in her pocket. "We'll save the rest for later, hmm?" She smirked suggestively. Cas just stared, wide eyed, unsure of what was happening. He wanted Dean, needed Dean to help him.

But as he turned in the direction of his friend, he found that the freckled boy had managed to smooth talk Lisa into "taking a walk" with him alone. As they headed off, Dean turned around to dance a ridiculous number that involved fist pumping the sky before resuming his conversation with Lisa.

As Cas tried to make sense of the hand that had slipped behind his jacket and was rubbing his back, another girl joined their group

"Oh Hell, more Angels."

Jo groaned. "Ruby, how wonderful of you to grace our presence."

The brunette crossed her arms over her chest. "Down, girl."

Their relationship with Ruby wasn't bad, or even tense. They just all found an excitement in playing up the whole rivals energy. 

Ruby's eyes ghosted over Cas and Jo before landing on Anna. "Well, well. Are you another Angel?"

Anna nodded, smiling hesitantly. 

Ruby regarded her thoughtfully before grabbing the redhead's arm. "C'mon. You look like you could use a little corruption," she said with a playful grin. Anna, for all her levelheadedness, followed Ruby without complaint.

Cas opened his mouth to complain, maybe order his sister back this instant, when Meg placed a finger over his lips. Helpless, Cas pleaded with his eyes to Jo, who sighed reluctantly and headed off in the direction of Anna and Ruby.

Meg slid in front of Castiel, biting her lip as she ran her other hand over his chest. She brushed her thumb across his lip, pausing when it dragged over the piercing.

"You seem pleased," he said.

"I got you alone, didn't I?" she grinned triumphantly. "And . . ." her eyes drifted to his lips, which he licked self consciously, "You look sexy with that on your lip." 

Cas didn't know how to respond to her forward advances. His body kept betraying his mind. Meg must've sensed Cas's uncertainty, because she waved the flask in his face again. "A little whiskey never hurt anybody."

"I doubt that's true. There's alcohol poisoning, and drunk driving of course, not to mention—"

"Drink, Clarence," Meg interrupted. And Castiel did.

He gulped down the amber liquid as Meg bit her lip, that smile a constant expression of hers. Meg may be just what he needed to straighten out this ridiculous crush on his best friend.

Somehow, they ended up back in the barn. Meg was dancing in front of—no, on Cas—sliding up and down his body in the most seductive way possible. Her hands continued to map out his body, sometimes bunching up bits of t-shirt in her fists. At one point, she grabbed his ass, and Cas felt something. He looked down at her, judgement clouded with the haze of alcohol, and leaned closer. Out of the corner of his eye, he noticed Dean dancing with Lisa just as close, if not closer than Cas and Meg. In a split second decision that he would probably regret later, Cas picked up Meg and slammed her into the wooden post to his right.

Blocking out the multitude of angry voices in his head, Cas shoved his mouth onto Meg's.

For a split second, it didn't seem like she would kiss back, and his body flooded with embarrassment. Kissing someone so Dean would notice was one thing, but having that person reject you was humiliating.

But then Meg opened her lips and pushed her tongue against his, hands pushing up the fabric of his shirt so she could rake her nails against the bare skin of his back. Cas wrapped her hair around his hand and tugged her head back so he could deepen the angle.

When a couple people started cheering, and a few shouts of "Get a room!" erupted around them, Meg pushed lightly on his chest to slow him down.

"I think they're right," she whispered in his ear. 

Not bothering to analyze his situation, or the situation he was getting into, Cas allowed Meg to tug him along. He met Dean's stare over the heads of the partygoers, and his friend had a storm cloud of emotions on his face that Castiel couldn't decipher because his brain was so fuzzy. Nevertheless, that last thing Cas saw before he left the barn was Dean shooting him a thumbs up and a wink.

The dark stumble of a walk outside was a blur, although Cas thought they may have stopped to make out against the porch railing before Meg pushed him up the rest of the stairs. They stumbled down a hallway, feeling for doorknobs that weren't locked, before one gave way and they tumbled into what looked like a guest bedroom.

Except it was occupied. By a pretty girl reapplying her makeup. She looked up in surprise at the two people who had just crashed her silence. 

The three had a five second stare off before Cas's eyes focused enough on the girl to make out who it was. "April?" he asked.

"Uh, yes. Castiel?"

He could only nod sloppily, one arm slung over Meg's shoulder.

Meg glanced between the two of them. "Clarence, you know this girl?"

Cas nodded again, incapable of more than one word of speech without slurring.

The brunette looked April up and down before sidling up to her. "Well, sweetie, blue eyes here and I here were about to get into a little bit of mischief. Of course, you're welcome to stay. We couldn't mind," she spoke in a voice like smoked honey that Cas supposed was her sexy voice. 

"Would we, Clarence?" 

Cas realized the question was directed at him, and he nodded. Meg chuckled, turning to April. "Trust me, sweetheart. He wouldn't mind."

Castiel watched April through hooded eyes, figuring she'd shake her head politely and shove out the door. But to his slightly dulled surprise, she hesitantly started to lift her head. 

Meg's eyes widened briefly before she schooled her features back into the sultry persona she was using. 

"This night just got a whole lot more interesting," she giggled, grabbing April's hand and pulling her into a gentle kiss. Cas stared, unsure of himself, until Meg led April over to the bed and pounced on Castiel. He barely registered the sink of the mattress as he fell onto it, and he found that at least one part of his body seemed to enjoy the double attention.

As the articles of clothing became sparser, Cas had to bite back Dean's name when a pair of lips clamped down on his collarbone.

All of the touches, kisses, and moans coalesced into a state of bliss that overtook his senses.

He felt. He moved. He blacked out.

**Notes for the Chapter:**

> I'm sure some of you were hoping I'd throw Dean into the threesome instead of April, but in the timeline of my story it's too early for that. However, there is a strong possibility of a threesome that could involve Dean and Cas, but it will be later in the story.  
> Also, sorry there's not much smut. I don't really like writing straight porn lol.  
> Chapter 7 will pick up rather shortly after where this one ended...


	7. Desirous of Everything at the Same Time

**Summary for the Chapter:**

> Lots and lots of miscommunication that is resolved at the end of the chapter.

Cas's eyelids were glued shut. Or at least, that's what they felt like when he tried to crack them open. Eventually he just reached up to rub at them until he could see and take in his surroundings.

He was on his back in a bed—not his own—and the sheets were rumpled disastrously. The blinds were open, letting in a maddening amount of light that cut like daggers directly through his eyeballs. His head was pounding, his stomach cramped with nausea, and his throat was as dry as sandpaper. His first thought was water. His second was toilet.

He fumbled with the blankets bunched around his waist until he managed very gracefully to fall out of the large bed and onto a cold hardwood floor. He groaned, rubbing his face to try to coax some life into it. With great difficulty, he managed to heave himself up off the floor, pushing into the bed for balance. 

A soft sigh sounded from under the blankets, and Cas turned a confused eye onto a pile of dark waves peeking out from under the sheets. Very slowly, he backed away from the bed until his back hit the wall by the door. The events from the previous night were starting to return with painful force.

As he scrambled to remember everything that went down, the adjacent bathroom door creaked open, letting out a freshly showered and dressed April Kelly.

Wait, April Kelly?

She barely spared him a glance, offering only a curt nod, before reaching past him for the door handle and practically flying away from him. Cas stared dumbly at the open door and April's retreating figure when another body suddenly appeared, narrowly missing the redhead's speedy getaway. 

Dean stared after the girl with eyebrows that had inched up almost comically. Cas might have laughed if he didn't feel like vomiting all over his best friend.

The Winchester then turned to Cas. He immediately snapped his head up to the ceiling, however, color rising to his cheeks. Cas, still apparently unable to speak, continued to stare.

"Dude," was all Dean said.

Cas squinted, rubbing his throbbing temples. "What," he croaked out, voice raspy and dry. He tried again, "What is the matter?"

Dean gesture vaguely at Cas, eyes flicking down for a second before returning to studying the cracks in the ceiling.

"Pants, dude," he finally hissed, looking scandalized. Cas glanced down to see that he was not, in fact, wearing any clothes at all. He must've been really hungover, because that realization didn't even bring him embarrassment. There he was, standing naked in front of Dean Winchester, a fantasy he may or may not have dreamt before, but it was not at all the circumstances he had imagined.

"Oh," was all he managed to get out. Then, "I think I'm going to throw up soon."

Dean sighed. "Do you have your boxers nearby?"

"I—probably?"

Dean made a move to push past Cas before remembering his friend's glaring nudity. The blush made a comeback. "Can you put them on?" he gritted out. "Now?"

"Oh. Right. Yes, um, of course." Cas was having a hell of a time figuring out how to speak English. He backed away from the door, scanning the mess of a bedroom before his eyes landed on a crumpled gray heap that was his boxers at the corner of the bed. He quickly snatched them up and pulled them on, reality beginning to set in as he felt the first waves of shame and embarrassment.

But then he clutched his stomach, remembering his nausea. "Dean," he mumbled.  
His friend shot over and ushered him into the bathroom, shoving him onto his knees in front of the toilet just as Cas started retching, emptying his angry stomach as his eyes watered.

"Ugh," Dean grimaced, leaning in the bathroom doorway. "You're lucky I'm your friend because this is disgusting."

Cas flipped him off, earning a chuckle, before vomiting again, stomach contracting to push the offensive content into Lisa's toilet. He flushed, stumbled over to the sink, and rinsed his mouth at least a dozen times.

"So," Dean began, "You had sex with April?"

Cas froze as he remembered the girl Meg had invited to join them. "Yes."

Dean seemed surprised at the easy confession, but he shook it off and walked back into the bedroom, motioning for Cas to join him, presumably in gathering his things. But as they walked by the bed, a lump beneath the sheets rolled around before a groggy head pulled back the blanket. "You two knuckleheads gonna leave yet or what?"

Dean gaped at the brunette. "You had sex with Meg?" She sneered at him.

". . . Yes."

"You had sex with April and Meg?"

"Um, yes?" It came out like a question. 

Meg rolled her eyes. "Guy's a kinkier bastard than I thought."

Cas started to protest that it was her idea, that he was too drunk to really comprehend what he was agreeing to, but then she stood up, stark naked, and looked around the room.

"Oh my god," Dean complained, throwing his hands in the air. "Does no one have any sense of modesty here?"

"You're one to talk, Winchester," Meg shot back as she slipped into lacy black panties and clipped her bra on. "I highly doubt your activities last night were conservative."

Cas, despite the distracting headache that refused to fade, managed to feel an ugly twinge of jealousy. A feeling, he mentally reminded himself, that was entirely ridiculous, childish, and hypocritical of him.

Almost automatically, an easy grin slid onto Dean's face as he remembered his own debauchery. "Ah, yeah. Goddamn, that girl is flexible."

Meg rolled her eyes as she stepped into jeans and threw on a purple tank top. "Well I've had enough of your testosterone, so if you'll excuse me, I need to get to my internship."

Cas remembered his manners. "Oh, where do you work?"   
"Mental hospital," Meg answered while brushing through her tangles, "Figured it'd make me feel less crazy."

She paused on her way to the door, "Besides, I like the patients."

Dean raised an eyebrow. "Would you look at that. Bitch has a heart."

"Not for you, pretty boy," Meg snapped and disappeared out of the room.

"Charming," Dean commented. "You really know how to pick 'em, Cas."

"I ... Last night was ..." Not comprised of the person I would have picked. "Informative," he settled on instead.

"But I need to get rid of this headache," he added.

Dean chuckled before tossing a white bottle his way. "Got you covered."

"You always do," Cas said without thinking, only realizing how sappy it sounded after. They stared at each other in silence for longer than necessary before Dean broke the eye contact to rub at his neck and Cas unscrewed the lid on the ibuprofen.

"Now come on, get dressed. We gotta find Jo and Anna," Dean told him.

Cas straightened, panic flooding his system. "Oh god, Anna. How could I have been so stupid? She left with Ruby and I stayed with Meg when I should have been watching her ... damnit!"

"Woah, woah, hey, Cas. It's okay. Anna knows how to take care of herself, honestly. And as bitchy as Ruby can be, she seemed to honestly be committed to helping Anna. That girl is genuine, occasionally." 

Cas refused to let himself feel relieved. Not yet. Not until he could see his little sister, his responsibility, with his own eyes.

He hurriedly dressed himself, wrinkled his nose at his reflection, and nodded at Dean. "Let's go."

They walked through Lisa's fairly sizable house, poking their heads into rooms and interrupting irritated, tired partygoers who were either resistant to waking up or in the middle of attempting to look decent and innocent as they prepared to head home to inquisitive parents. 

There weren't a ton of people who stayed the night; there may have been around fifteen or so composed of those who passed out drunk the night before, immovable, and those who Lisa was closest to or had invited. Cas wasn't any of those, really, but he figured that because of Dean, their little group just sort of stuck around.

When the search upstairs ended up futile, Dean led Cas downstairs into the living room where two people were still left on the couch. One was Ruby, folded into the couch with her hair draped over the arm and legs folded up to her chest.

The other was Anna, to Castiel's immense relief. She was curled up on the opposite end with her feet pressed against Ruby's. As Cas allowed himself to calm down now that he could see for his own eyes that his little sister was unharmed, Dean, asshole that he was, smirked before bringing his hands together in loud, successive claps.

"Rise and shine, ladies! Sun is out, birds are chirping, and it's time to get your lazy asses up from the couch! Carpe diem!" He shouted as Ruby shot up, rubbing sleep from her eyes, and fixing Dean with a glare that easily said she'd rip him to shreds if she could.

"Will you shut your goddamn mouth?"

Anna fluttered her eyelids open, groaning as she tried to brush tangles out of her face and stretch out her cramped legs. "What'd we do to you?" She grumbled.

Dean continued to smile like an idiot before turning to leave. "We're getting ready to go. Anyone know where Jo is?"

"Present," a voice scratched from the kitchen.

Jo emerged with a cup of coffee in her hands and a guy trailing her like a lost puppy. "What are we waiting for? Momma's gotta get some beauty sleep."

"You don't need it," the guy beside her said. Everyone in the room must've collectively raised an eyebrow. Ruby looked like she wanted to puke on his shoes. Jo just sighed in exasperation.

"Andy?"

"Yes?" He responded immediately.

"Go home," Jo instructed. 

Andy's face fell slightly before nodding. "Well, uh, you can call me or whatever."

Jo took another sip of coffee. "I'm definitely capable of pressing buttons."

Her sarcasm hit record highs in the mornings, something Andy seemed obvious too. "Oh good," he paused, as if waiting for Jo to say something. She stared at her mug. "Well, have a good weekend!"

"Goodbye, Andy."

He muttered a few more pleasantries before stumbling out the front door. Jo breathed a sigh of relief and sunk into an armchair. 

"Good god, I thought he'd never leave me alone."

"That bad in the sack?" Dean asked.

"That's the thing. We didn't even have sex. I just had the misfortune of striking up a conversation with a hot guy who turned out to have attachment issues. So I had an idiot glued to my hip the whole night." She turned forlorn eyes on her caffeine. 

The room was silent after that. It seemed no one had truly woken up except for Dean, a strange fact considering he was the least likely to be a morning person. Must've been a pretty amazing night with Lisa, Cas reasoned, ignoring the churning in his gut.

"O-kay," Dean drew out the 'o,' "This party is obviously over. Time to go home."

Anna said goodbye to Ruby and the four of them followed Dean to where he'd parked the Impala. When they were halfway down the porch steps, Lisa burst out the front door. Cas stared as she leaned down to whisper something in his ear, his hand gripping her waist as he smirked at whatever she told him. Cas caught Dean's drawl of "sure thing, sweetheart," before they kissed briefly. She waved goodbye to the rest of them, and Dean's smirk stayed plastered on his lips all the way to the car.

"That good in the sack?" Jo echoed Dean's earlier question.

He paused, licking his lips. "She's an assistant yoga instructor," Dean said with reverence, as if that were the answer to all the world's problems.

"You gonna see her again?" Cas asked as they pulled out of the driveway.

"Nah," Dean answered.

The car raised their eyebrows in shock. "No?" Jo repeated.

"Look, she was great and all, and she wants to do it again, but I know where that leads. I don't have time for that shit."

"Did your mom not love you enough as a child?" Jo teased.

Dean rolled his eyes. "Shut up, blondie," he shot back, knowing she hated that nickname. And the conversation lulled as they drove home. Jo saluted them as she crawled out of the car like a soldier preparing for battle. Knowing her mom, she probably was.

Cas walked with Anna to their house, turning around to wave at Dean. "Cas, wait," Dean called.

Castiel leaned down, propping his forearms on the car door through the open passenger window. Dean rubbed his face which was red for some reason. "I, uh, I know that last night was, um, your, you know ..." he trailed off before clearing his throat, "your first time. And so, if you, uh want to talk or whatever, you can."

Cas stopped breathing for a second as the blood rushed to his ears. Shit. He was going to have to tell Dean about what happened That One Night. The night from four months ago that he hadn't mentioned to a soul, especially not Dean. Or maybe he didn't. Maybe if he never admitted it, it wouldn't be true. Dean stared at him, waiting for a response, probably interpreting Cas's silent awkwardness as a reluctance to talk about losing his virginity, obvious to his best friend's true inner turmoil.

But if he never talked to Dean about That One Night, then it would continue to rattle around in his brain and send him into even more random identity crises. Cas took a deep breath as he made a split second decision that he would probably back out of later.

"Could I ... come over later?" 

Dean smiled easily, expecting a recount of Cas's wild sexual endeavors the night before. "Of course, man. You don't even have to ask."

Cas nodded shakily before standing to leave. His best friend threw one of his characteristic three fingered waves and pulled away to park in his own driveway. 

Catching up to Anna, the siblings walked into an uncharacteristically quiet house, so Cas figured Gabe was asleep and Lucifer was out back in the garden. Michael, despite owning a swanky apartment (or at least, as swanky as one could find in the already small downtown of rural Kansas), typically hung around home a lot. Probably to make sure his siblings stayed on e straight and narrow since Chuck wasn't much of a role model. 

"Anna," Cas started since they were alone.

"Castiel, stop. I don't need you babysitting me," Anna snapped.

"I'm not—I don't—" Cas sighed, earlier panic momentarily forgotten as he tried to get through to his sister, "I'm just trying to keep you safe, okay? I'm your big brother. That's what I do. I'm sorry if you hate it, but I couldn't stop even if I tried. And I know it's hard without mom," Anna's eyes glistened at the mention, "and you're stuck with a house full of guys who act like animals and probably smell bad and yell a lot and Michael's an asshole and dad spends all day writing, but you're still the baby of the family. And it's our job to protect you because you hold this family together. You always have. Without you, I'm sure it'd be an apocalyptic fight for control."

Anna sniffed, and Cas realized she'd started silently crying. "Wait, no, that wasn't how it was supposed to go. It was supposed to cheer you up—"

His words were cut off with an oomph as Anna slammed into him with a hug. "This is why you're my favorite," she whispered. 

Cas rolled his eyes. "Sure. You say that to all of your brothers."

She smiled sweetly at him before brushing past to head up to her room. Cas was suddenly conscious of the greasiness of his hair and stench of alcohol and traces of sex that clung to his clothes and skin. He craved a shower, needing to wash off whatever last night was.

As the scalding water rushed over his naked body, Cas leaned against the tile and closed his eyes, trying to steady his pounding heart. He knew it would happen eventually: he would need to confront his own self about That One Night. It had been a constant drag, remembering what happened. Every day he he tried to push it down, write it off as nothing. If he convinced himself if never happened, maybe he would eventually believe himself and forget about it. Maybe he could be normal. Maybe all his recently increased thoughts and feelings about Dean could then be written off as aftershocks of what he had done, outlets for his body to make sense of that night.

Because Cas didn't lose his virginity the previous night to Meg, of April, or whatever had happened exactly. He'd lost it four months before to Balthazar, the cocky, smooth talking British college student he'd met at a party Gabe dragged him to one night to "socialize him." 

The details were a bit hazy, but he remembered drinking out of nervousness from unfamiliar surroundings. He'd backed himself into a darkened corner of a hallway, near the bedrooms. The apartment was loud, it was packed too full, and then there was a smirking face in front of him.

He had, of course, had those passing thoughts about Dean for the past couple years, but he never put much weight to them. They freaked him out, but he reasoned they were just the results of hyperactive teenage hormones. 

"You're looking terribly bored there," Balthazar had cut in. 

Cas looked up in surprise at the intrusion. "What? Oh, no, it's a great party." He winced at he flatness of his words.

The Englishman raised his eyebrows. "Not very convincing, are we?" He folded his arms over his deep black v-neck. Arm muscles strained against the overly tight fabric, and Cas found his eyes drawn to the movement. 

Cas, unsure of what to say, raised his cup to his lips and took a giant gulp. He yelped in surprise when Balthazar plucked the drink out of his hands to sniff it. "Oh, god, this isn't even the good stuff." He set the drink on an end table before disappearing momentarily into the room behind Cas and producing a bottle of something fancy that Cas wouldn't have recognized if he tried. "Here, have some of this instead."

Castiel eyed the bottle warily, hesitant to take drinks from strangers.

Balthazar chuckled. "Don't worry, I haven't drugged it or anything. Just didn't want everyone drinking my real alcohol."

Cas's brain caught up with him then. "This is your party?"

Balthazar bowed slightly. "Guilty. Although, I must say I have no idea who you are or why you're here, but I'd love to find out."

And then there were long fingers curling around Cas's waist and the man he'd met only minutes before was suddenly much closer. He shivered despite his confusion and weak attempts to reason with himself that he was 100 percent straight. Or at least, 99.9 percent,

Balthazar leaned down to whisper in Cas's ear, "How about we talk about it in my bedroom?"

And it was like Cas's body had detached itself from his rational brain. His heart rate had sped up, his skin was thrumming with the thrill of having someone pressed so close. Possibly the biggest indicator that his sexuality was very different from what he originally imagined was the way his lower body reacted embarrassingly quickly to the other man's advances. Balthazar caught on, smirking as he placed hot, open mouthed kisses along Cas's throat, inching his way up to his lips. 

"I never got your name. Need something to cry out while we're sweating together, right?"

Cas stopped resisting after that. "Cas ... Castiel," his voice came out in short gasps as Balthazar's hands gripped his ass.

"Alright then, Cassy. Let Balthazar take care of you."

So he let go. He let himself be led behind closed doors, let Balthazar strip him down until he was more exposed than he'd ever been in his life, let another man touch him, stretch him, bring him to orgasm.

Cas wasn't very loud; he was unexperienced and still slightly embarrassed on how to act. Balthazar kept his exclamations at a low volume too, but that didn't mean he didn't fill the silence. Cas found he was pretty turned on by the stream of curses that flooded out of Balthazar's mouth as well as slightly amused at how such a proper voice could emit such dirty sounds.

But mostly, he was awkward. He didn't know what to do, how to make Balthazar feel good. He just laid there and took it, ignored the initial discomfort, and managed to enjoy it at the end. All in all it really wasn't bad. He chalked the strangeness of it up to just inevitability because it was his first time.

However, as soon as Balthazar rolled off of him, satisfied, and tossed away the condom, panic set in. He'd just been fucked. By a guy. Did that make him gay? Was he forever cursed to only have sex with men? Would everyone just look at him and know he'd had a dick up his ass? 

Cas managed to get dressed faster than he thought possible, wincing at the pain in his ass. He mumbled some sort of halfhearted excuse or thank you to Balthazar, he couldn't remember anymore, and shot out of that apartment so fast it felt like he was a cartoon character. Except he wasn't laughing, he was terrified. 

Not bothering to find Gabe, he ducked into the nearest gas station and made a beeline for the bathroom. He sat on the toilet for a good twenty minutes, clutching his stomach and waiting for the soreness to subside. When it didn't, he pulled up his pants, splashed his face, and locked away the experience, pushing down, most importantly, the fact that besides the awkwardness and slight discomfort, besides the fact that it upturned everything he thought he knew about his sexuality, he'd enjoyed it. He packed it away with every other passing thought he'd ever had about another man, namely Dean, because now he'd actually acted on those fleeting desires. 

And it scared the crap out of him.

So when Dean commented on the fact that he looked like he was walking with a stick up his ass the next day, Cas violently shoved down his nausea and laughed it off, saying he fell out of a tree trying to grab his backpack that Lucifer had thrown up in the branches. 

Now, Cas turned off the water and dried of, rubbing shaking hands over his face as he got dressed and spent the next five hours pacing, second guessing his decision, showering a second time, and walking tv until his eyes burned. Eventually, he got his shit somewhat together and walked heavily over to Dean's, dread slowing his gait as he nervously moved around his piercing with his tongue. 

Mary answered the door, smiling sweetly at Cas. "Cas, honey, don't bother knocking. You can just walk right in." She said the same thing to him every time he came over, but Cas must've had some deep seated politeness ingrained into his personality that rendered him unable to barge into people's homes.

"Of course, ma'am," he answered as usual. Only this time, he was wringing his hands nervously, wondering if this may be the last time he's welcome. Dean may be disgusted at the sight of him after tonight. But it was too late for Cas to back out. He'd never be able to push everything down after today, not when it boiled on the surface, threatening to tear straight out of his skin. 

Mary waved him in. "Dean's up in his room." He started to head up when she stopped him. Oh god, he thought. She knows. She knows and she's going to tell me that this is a terrible idea, that he'll hate me.

But Dean's mom smiled mischievously. "Is that new?" She asked, eyes on Cas's lip piercing.

"Oh, uh," he shifted self consciously, talking fast, "I guess I was wanting to try something different, and my sister talked me into it, and—"

"Relax, Castiel. I think it looks cool," she insisted with a smile. 

"Totally. Looks badass," Sam interjected as he walked past, gangly limbs swinging. Cas could've sworn the boy had grown two more inches overnight.

"Language," Mary scolded. 

Cas excused himself and trudged up the stairs to Dean's room. Loud Metallica seeped under the door crack, and Cas tried the door to see if it was locked, knowing Dean would never hear a knock. 

His friend was on his back on the bed, eyes trained on the tv in his room as he flipped his thumbs over the xbox controller, blasting holes in the heads of attacking zombies. He glanced over at Cas and grinned apologetically, pausing the game so he could turn down the music.

"Hey man, what's up?"

Cas cleared his throat and sank to the floor, leaning his back against the bed. He had to do it. Had to get it over with. At least this way, he wouldn't have to see Dean's expression morph into one of surprise and disgust.

"I, um, wanted to talk. About ... you know ..." Except Dean didn't know. Not yet.

Cas felt the bed shift as Dean hopped off it and slid down next to Cas. "Of course. Hey, I'm listening."

Cas took a deep breath, his semi practiced speech disappearing from his mind. "I lied," he blurted out, sneaking a glance over at Dean. His friend furrowed his brow in confusion.

"You lied? About what? Last night?"

Cas nodded. Realization flickered across Dean's face.

"Look, Cas. I'm sorry if all my shit made it seem like I was trying to pressure you into putting out. I just ... god, I'm such an ass. I never meant for that. You know I don't think you're a loser or anything for not having sex yet, right? I don't give a damn about that. You're still my best friend. I just feel like such a dick for making it seem like you needed to sleep with someone."

Now it was Cas's turn to be confused. "Wait, what?"

Dean nodded. "I really am sorry. But I mean what I said. Don't feel like you have to make that shit up. It'll happen when it happens. You didn't have to fake an elaborate threesome deal; I'll still like you either way. Even if it does end up being Meg."

Cas's mouth dried out. "Dean, no."

"Okay, I mean it doesn't have to be Meg, obviously. I'll stop bugging you about April, too. There's no written law that says you have to lose your virginity before you're eighteen. I mean, uh, whenever you feel ready. Shit, I'm not exactly the poster child for this sort of thing but—"

"Dean!" Cas practically shouted in order to shut up his rambling.

Dean glanced at him in surprise. "What? What did I say?"

"I did lose my virginity."

Poor Dean looked even more lost. "But I thought ..."

Cas took a deep breath and fixed his eyes on his hands clenched in his lap. "I did lose my virginity," he repeated, "But I didn't lose it last night."

Dean was silent, so Cas went on. "And I didn't lose it to Meg." When Dean still didn't say anything, Cas took that as encouragement to go on, so he did. "Just hear me out."

He told the whole story of That One Night, minus all his inner turmoil throughout the whole process and with a very removed tone. He gave Dean just the cold, hard facts, careful not to reveal too much in case it worsened his best friend's revulsion.

When he finished, he worried his lip relentlessly as the silence stretched longer than necessary. His heart was beating so fast that it actually hurt, and the blood rushing through his veins roared in his ears.

Finally, Dean broke the silence. "That motherfucker," he growled. Cas whipped his head to the side in shock. Dean's features were contorted in anger: his jaw was clenched, his eyes hardened, and his fists twitched like he wanted to punch something. Then Dean stood up abruptly, marching aimlessly across his room.

Bewildered and wary of what was going on, Cas stood cautiously and followed Dean's movements. This was not even a reaction he'd considered. Disgust and revulsion and anger at Cas, yes, but directed at Balthazar?

"Um, Dean?"

"No, Cas. Don't. Don't try to defend him. I can't believe that arrogant, British prick. God, I wish I could beat the living shit out of him. I mean, taking advantage of a high school student? An underage high school student? Jesus fucking Christ," he paused his ranting briefly, "Wait, does Gabriel know? If that dick is defending his friend then I swear, there are going to be a lot of punches being thrown."

Cas's eyes widened in shock when he realized Dean thought that the sex wasn't consensual. He bit his lip so hard he drew blood, anxiety flooring him at the fact that he literally had to spell it out for Dean.

"Dean," Cas did yell this time, nails digging into his palms. Why was this getting so out of hand?

Dean finally stopped, anger melting into concern as he looked at Cas. 

Castiel shook his head back and forth multiple times. "God, I—I didn't think I'd have to say it. Dean, you've got it all wrong."

Dean frowned, opening his mouth as he started to interrupt, but Cas beat him to it. "I liked it, Dean. Okay? I fucking liked it. And it was because I liked it that I didn't tell a goddamn soul because I didn't want to be that one gay kid in Lawrence. I wasn't ready to deal with that ridicule. And I couldn't even figure out what I wanted. I still don't. I had sex with Balthazar and I had sex with Meg. Maybe I'm bisexual, I don't fucking know. I don't know." His voice cracked at the end and he started when he felt a tear roll down his cheek. He was crying now?

He glared at the floor in shame, hoping it would give him an answer about who the hell he was, because he definitely didn't know.

And then there were strong arms wrapping around his trembling body and forcing him into a bear hug. He tried to back out of it, not believing that Dean could still look at him, let alone touch him, but his friend only squeezed harder. He thought he heard Dean whisper something like, "God, I'm an idiot," but it was hard to hear with his face pressed into Dean's shoulder. 

And then Dean spoke louder so that Cas could hear him, loud and clear. "I know who you are," he said firmly, "You're my best friend. And I don't give a fuck about anybody else's opinion."

Cas finally let himself melt into Dean's arms, wrapping his own around his friend's torso. It was more than he deserved, more that he thought possible. But he was going to hang on while he could.

**Notes for the Chapter:**

> Sorry this took me so long to post. I started college and that's been stressful. But I made this chapter longer so hopefully that makes up for it. Please let me know what you think so far and if there are any discontinuities I need to fix. Also, I'm totally open to suggestions!

**Author's Note:**

> I love Jack Kerouac, and I know Supernatural was somewhat inspired by the Dean and Sal characters from On The Road. So, I'm going to theme my chapter titles and content with his various poems and works.


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